South to engage in espionage and intelligence-gathering activities were
unparalleled in the history of the relatively young nation. Although
daring, these efforts were often quite amateurish by modern standards.

The physical environment of America greatly facilitated covert activities.
With America as the "melting pot" of the world, people
throughout the nation represented every race and nationality in the world.
Unionist and secessionist alike came from every corner of the country and
both sides consisted of people of every race, creed, and color. Visually,
covert combatants could not be easily identified one from another.
Americanized English was the common language, but even with many regional
dialects, there were few specific speech patterns unique to either side.
State or region of origin was no guaranty of which side one might take in
the conflict.

People were free to travel practically at will. Boundaries between Union
and the Confederate held areas existed primarily as lines on a map and
posed no controlled barrier to travel. Many major rivers traversed the
land north to south. Major mountain ranges trended north/south. Railroads
and roadways had been developed in all directions. Getting to and from one
area to another was relatively easy and borders were difficult to control.
Spies and agents were free to roam practically at will restricted more by
their own skill and courage than any other factor.
With travel being relatively unimpeded it was fairly easy to pass written
or memorized verbal messages through the lines. Both sides developed
methods to encrypt messages using various forms of alphanumeric sequence
codes and cipher wheels. The telegraph was the leading communication
technology of the period. Anyone with a portable key set could tap into
any line and monitor, receive, and send massages often confusing and
countermanding orders being sent over the wire. Confederate cavalry leader
John Hunt Morgan habitually included a telegraph operator on his staff
just for this purpose. Hunt was so daring as to send a message to the U.S.
Commissary Department over telegraph lines operated by the U.S. Army
complaining about the quality of mules being supplied to units opposing
him and being captured by his men. Requisitions for supplies were often
submitted in similar fashion in anticipation of capture from the
adversary.

Hot air balloons were introduced by both sides for observing troop
movement and disposition, spotting artillery fire and relaying signals.

The Confederacy led in the development of "infernal weapons"
such as mines and torpedoes that were, at the time, considered violations
of the rules of war as they acted upon unsuspecting prey. The concept of
these devices was relatively simple in including a black powder charge
within a watertight container and a detonation device. The Brooke buoyant
torpedo consisted of a metal dome with contact detonators on top mounted
on a metal conical shaped container attached to a wooden spar anchored on
the bottom of a waterway. At times a Turtle torpedo containing as much as
100 pounds of explosives would be attached by wire to the base of the
spar. Attempts to remove the adjacent buoyant torpedo would pull the wire
and detonate the Turtle. Other torpedo designs included floating
containers detonated by contact or electrical charge from a shore based
agent and free floating drifting mine detonated by an attached propeller
mechanism after coming to rest against the hull of a ship. River and sea
torpedoes could be placed by agents or troops in advance of the arrival of
the opposing force.

However, the Coal torpedo required placement in a fuel storage depot or
bunker by an agent and quite often in the presence of the enemy. The Coal
torpedo was made of a hollow chunk of iron cast to look like a piece of
coal. The fake coal contained a charge of powder and was coated with tar
and coal dust and exploded with tremendous effect when fed into the boiler
fire of a steam engine either on board a ship, on a train or in a factory.

Agents on the ground were the backbone of the espionage and intelligence
gathering efforts of the period. Unfortunately the identity of most of the
agents of the conflict was lost as many operated under multiple names;
records were often poorly kept, and lost or intentionally suppressed or
destroyed. Contraband and escaped slaves served as a primary source of
intelligence for the U.S. Army. However, a former barrel maker, sheriff
and native of Scotland organized a detective agency in 1850 that served
the Union effort extensively and is still in business today. Alan
Pinkerton formed the National Detective Agency and gained fame by foiling
a plot to assassinate President Lincoln in 1861 and went on to create the
secret service of the U.S. Army. Neither Pinkerton nor his agents had any
training in intelligence gathering and were notorious for their tactics
and the over-estimation of Confederate troop strength. During the
Peninsula Campaign over the spring and summer of 1862, General G. B.
McClellan (U.S.) had advanced the Army of the Potomac and its 108,000
effectives to within sight of the church spires of the Confederate capital
city—Richmond, VA. However, based on intelligence gathered by
Pinkerton that suggested a potential opposing Confederate force nearing
200,000 who were well fortified with reinforcements en route, the general
paused to plead his case with Lincoln for more troops. In fact, General R.
E. Lee never had more than 85,000 effectives under his command during this
time, as his smaller force drove the Federal horde before him in full
retreat. Pinkerton's unintended misinformation may well have served
the defense of the Confederate capital city better than the mythical
reinforcements that were not coming. It would be some two and a half years
before the U.S. Army would get that close to Richmond again. Yet,
Pinkerton and his organization remained in Federal service well beyond the
war. Much of Pinkerton's information came from criminals and
escaped slaves who lacked the skills of espionage and were thus, prone to
exaggeration, along with agents who may have spent more time enjoying
Richmond's pleasures than actually counting troops in the field. In
time, the Confederates learned to appreciate the value of misinformation
and intentionally sent men forward to become captives of the Federal
forces and spread inaccurate information.

American culture was still quite Victorian in many ways during the
1860's. Women agents had a decided advantage over their male
counterparts, as they were not likely to be as roughly interrogated or
possibly executed upon discovery. Both sides took full advantage of the
opportunity.

Belle Boyd shot and killed one of two drunken Union soldiers who had
entered her Martinsburg, VA home on July 4, 1861. She was acquitted and
set free. Thereafter, Boyd voluntarily forwarded her written observations
of Union activity in her area to local Confederate authorities. During
General "Stonewall" Jackson's Shenandoah Valley
Campaign, Union troops occupied the town of Front Royal, VA where Miss
Boyd happened to be at the time. Observing the panic that developed among
the invading Federals upon their learning of Jackson's approach and
overhearing their plans to burn a large supply depot in town and the
bridges across the South Fork of the Shenandoah River as they retreated
northward, seventeen year old Belle decided to inform the Confederate
forces personally. Under fire from Union pickets, Boyd dashed several
miles to carry her knowledge to the approaching Confederate column. The
leading elements of the column then dashed forward to save the bridges
that later enabled Jackson to drive up the valley driving the forces of
Union General Nathaniel Banks before him and freeing the vital
area's food supply to Confederate purpose.

Belle Boyd continued her activities until arrested on July 29, 1862, and
was transferred to the Old Capital Prison in Washington, D.C. No charges
were pressed and she was released one month later, where upon she returned
to Richmond and continued her work as a spy. Later she was arrested aboard
the blockade runner
Greyhound
outbound for England but managed to persuade Federal Lieutenant Harding,
who had been placed as prize master of the captured ship, to permit
Confederate Captain Lewis to escape en route to Boston. Before the end of
the war, Miss Boyd and Lt. Harding married.

Elizabeth Van Lew, a native of Richmond, VA who had attended a
Philadelphia Quaker school, was an ardent opponent of slavery and
pro-Union. After the war broke out, Van Lew was granted permission to care
for Union prisoners. Many of the prisoners had observations of Confederate
positions and troop dispositions that they hoped to get back to Union
authorities. Miss Van Lew established a network of couriers, developed a
secret code, and began passing messages through the lines to Union forces.
Many in Richmond referred to her as "Crazy Bet" as she
hummed and mumbled to herself as she traveled the town, while believing
her sympathy for the Union was part of her mental illness. "Crazy
Bet" is credited with procuring for Mary Elizabeth Bowser, a former
slave whom she had freed before the war, a job as a house servant in the
home of Confederate President Jefferson Davis. Together, the two women
collected valuable information that was passed on to Union officers.
"Crazy Bet" managed to maintain her cover throughout the war
and was one of the first people to be visited by General U.S. Grant upon
the taking of Richmond. Later, President Grant appointed her postmaster of
Richmond though the people of the city shunned her once they realized the
harm she had rendered to the Confederate cause.

Emma Edmonds, who was able to join a Michigan volunteer company by posing
as a man, gathered information for her company by "posing"
as a woman.

Legends and folklore are rich with stories of individual daring and
accomplishment as agents and double agents during the Civil War, but
verifiable documentation is only available in a few cases. Some of the
best intelligence gathering opportunities came about as random luck.
Perhaps one of the most significant instances of pure luck delivering
critical information into the hands of the enemy was the discovery of a
copy of General R. E. Lee's order of march as he moved northward in
September of 1862. A note was found on the ground wrapped around three
cigars by Federal soldiers that contained details of the order of march of
General R. E. Lee's divided forces marching through the Shenandoah
Valley on their way to carry the war to the North on their home ground.
Some historians assume that a member of General D. H. Hill's
subordinate command dropped this bit of critical information. Union
General G. B. McClellan had been cautiously seeking the Confederate force,
and the discovery of General Lee's order of march enabled McClellan
to unexpectedly close on them and force an unplanned battle near
Sharpsburg, MD along Antietam Creek. The battle unfolded to become the
most deadly single day of combat in American history, and ended in a
tactical victory for the South in that its army escaped annihilation and
withdrew southward in good order after Union forces refused to attack the
following day. However, the North claimed a major strategic victory that
changed the nature of the war, and ended consideration of European
intervention on the side of the South.

Both the Union and the Confederacy had agents working throughout the
territory of the other. The Northern media proved to be of great aid to
the Southern intelligence gathering effort. Northern papers continually
ran articles describing current events, Union troop dispositions, and
future movement in such detail that undercover Confederate agents kept a
constant supply of daily newspapers heading south from major cities such
as New York, Philadelphia, and Boston to commanders in the field.

Spying was not limited only to opponents. There was considerable spying by
various political factions on their own battlefield commanders and faction
against faction. This was particularly true on the Union side where trust
between President Lincoln, the cabinet, prominent congressmen, and the
military staff was particularly low during the early years of the war, as
the search for a commander who could defeat the secessionists created
considerable turmoil. Many Federal commanders also dreaded the political
opponents in their rear as much as the combat opponents to their front, as
many officers were removed to satisfy public whim.